U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H21N
Molecular Weight 239.356
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENZPHETAMINE

SMILES

C[C@@]([H])(Cc1ccccc1)N(C)Cc2ccccc2

InChI

InChIKey=YXKTVDFXDRQTKV-HNNXBMFYSA-N
InChI=1S/C17H21N/c1-15(13-16-9-5-3-6-10-16)18(2)14-17-11-7-4-8-12-17/h3-12,15H,13-14H2,1-2H3/t15-/m0/s1

HIDE SMILES / InChI

Molecular Formula C17H21N
Molecular Weight 239.356
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Benzphetamine is a sympathomimetic agent with properties similar to dextroamphetamine. It is used in the management of exogenous obesity as a short term (a few weeks) adjunct in a regimen of weight reduction based on caloric restriction in patients with an initial body mass index (BMI) of 30 kg/m2 or higher who have not responded to appropriate weight reducing regimen (diet and/or exercise) alone. Presumably, benzphetamine produces its effects through mechanisms similar to amphetamine via induces synaptic vesicular amine transporter, but precise mechanism of action of benzphetamine is not known.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
BENZPHETAMINE HYDROCHLORIDE

Approved Use

Benzphetamine hydrochloride tablets are indicated in the management of exogenous obesity as a short term (a few weeks) adjunct in a regimen of weight reduction based on caloric restriction in patients with an initial body mass index (BMI) of 30 kg/m2 or higher who have not responded to appropriate weight reducing regimen (diet and/or exercise) alone. Benzphetamine hydrochloride tablets are indicated for use as monotherapy only.

Launch Date

1.14523203E12
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4.9 μg × min/mL
10 mg/kg 1 times / day multiple, intraperitoneal
dose: 10 mg/kg
route of administration: Intraperitoneal
experiment type: MULTIPLE
co-administered:
BENZPHETAMINE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
13%
BENZPHETAMINE unknown
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
80 mg 3 times / day multiple, oral (max)
Dose: 80 mg, 3 times / day
Route: oral
Route: multiple
Dose: 80 mg, 3 times / day
Sources:
unhealthy, 54
n = 20
Health Status: unhealthy
Condition: Obesity
Age Group: 54
Sex: F
Population Size: 20
Sources:
Other AEs: Gastrointestinal signs and symptoms, Dizziness...
Other AEs:
Gastrointestinal signs and symptoms (5 patients)
Dizziness (4 patients)
Constipation (2 patients)
Nervousness (5 patients)
Pruritus (1 patient)
Dry mouth (3 patients)
Chest pain (1 patient)
Headache (1 patient)
Malaise (1 patient)
Fatigue (1 patient)
Appetite disorder (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Appetite disorder 1 patient
80 mg 3 times / day multiple, oral (max)
Dose: 80 mg, 3 times / day
Route: oral
Route: multiple
Dose: 80 mg, 3 times / day
Sources:
unhealthy, 54
n = 20
Health Status: unhealthy
Condition: Obesity
Age Group: 54
Sex: F
Population Size: 20
Sources:
Chest pain 1 patient
80 mg 3 times / day multiple, oral (max)
Dose: 80 mg, 3 times / day
Route: oral
Route: multiple
Dose: 80 mg, 3 times / day
Sources:
unhealthy, 54
n = 20
Health Status: unhealthy
Condition: Obesity
Age Group: 54
Sex: F
Population Size: 20
Sources:
Fatigue 1 patient
80 mg 3 times / day multiple, oral (max)
Dose: 80 mg, 3 times / day
Route: oral
Route: multiple
Dose: 80 mg, 3 times / day
Sources:
unhealthy, 54
n = 20
Health Status: unhealthy
Condition: Obesity
Age Group: 54
Sex: F
Population Size: 20
Sources:
Headache 1 patient
80 mg 3 times / day multiple, oral (max)
Dose: 80 mg, 3 times / day
Route: oral
Route: multiple
Dose: 80 mg, 3 times / day
Sources:
unhealthy, 54
n = 20
Health Status: unhealthy
Condition: Obesity
Age Group: 54
Sex: F
Population Size: 20
Sources:
Malaise 1 patient
80 mg 3 times / day multiple, oral (max)
Dose: 80 mg, 3 times / day
Route: oral
Route: multiple
Dose: 80 mg, 3 times / day
Sources:
unhealthy, 54
n = 20
Health Status: unhealthy
Condition: Obesity
Age Group: 54
Sex: F
Population Size: 20
Sources:
Pruritus 1 patient
80 mg 3 times / day multiple, oral (max)
Dose: 80 mg, 3 times / day
Route: oral
Route: multiple
Dose: 80 mg, 3 times / day
Sources:
unhealthy, 54
n = 20
Health Status: unhealthy
Condition: Obesity
Age Group: 54
Sex: F
Population Size: 20
Sources:
Constipation 2 patients
80 mg 3 times / day multiple, oral (max)
Dose: 80 mg, 3 times / day
Route: oral
Route: multiple
Dose: 80 mg, 3 times / day
Sources:
unhealthy, 54
n = 20
Health Status: unhealthy
Condition: Obesity
Age Group: 54
Sex: F
Population Size: 20
Sources:
Dry mouth 3 patients
80 mg 3 times / day multiple, oral (max)
Dose: 80 mg, 3 times / day
Route: oral
Route: multiple
Dose: 80 mg, 3 times / day
Sources:
unhealthy, 54
n = 20
Health Status: unhealthy
Condition: Obesity
Age Group: 54
Sex: F
Population Size: 20
Sources:
Dizziness 4 patients
80 mg 3 times / day multiple, oral (max)
Dose: 80 mg, 3 times / day
Route: oral
Route: multiple
Dose: 80 mg, 3 times / day
Sources:
unhealthy, 54
n = 20
Health Status: unhealthy
Condition: Obesity
Age Group: 54
Sex: F
Population Size: 20
Sources:
Gastrointestinal signs and symptoms 5 patients
80 mg 3 times / day multiple, oral (max)
Dose: 80 mg, 3 times / day
Route: oral
Route: multiple
Dose: 80 mg, 3 times / day
Sources:
unhealthy, 54
n = 20
Health Status: unhealthy
Condition: Obesity
Age Group: 54
Sex: F
Population Size: 20
Sources:
Nervousness 5 patients
80 mg 3 times / day multiple, oral (max)
Dose: 80 mg, 3 times / day
Route: oral
Route: multiple
Dose: 80 mg, 3 times / day
Sources:
unhealthy, 54
n = 20
Health Status: unhealthy
Condition: Obesity
Age Group: 54
Sex: F
Population Size: 20
Sources:
PubMed

PubMed

TitleDatePubMed
Characterization of rabbit liver P450IIE1 synthesized in transformed yeast cells.
1990 Oct
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.
2003 Jan 1
The naturally occurring cytochrome P450 (P450) 2B6 K262R mutant of P450 2B6 exhibits alterations in substrate metabolism and inactivation.
2005 Jun
Resonance Raman studies of cytochrome P450 2B4 in its interactions with substrates and redox partners.
2008 Mar 25
Ligand diversity of human and chimpanzee CYP3A4: activation of human CYP3A4 by lithocholic acid results from positive selection.
2009 Jun
Patents

Patents

Sample Use Guides

Dosage should be individualized according to the response of the patient. The suggested dosage ranges from 25 to 50 mg one to three times daily. Treatment should begin with 25 to 50 mg once daily with subsequent increase in individual dose or frequency according to response. A single daily dose is preferably given in mid-morning or mid-afternoon, according to the patient's eating habits. In an occasional patient it may be desirable to avoid late afternoon administration. Use of benzphetamine hydrochloride is not recommended in individuals under 12 years of age.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Jun 25 23:07:50 UTC 2021
Edited
by admin
on Fri Jun 25 23:07:50 UTC 2021
Record UNII
0M3S43XK27
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BENZPHETAMINE
HSDB   MI   VANDF  
Common Name English
(+)-BENZPHETAMINE
Common Name English
BENZFETAMINE
INN   WHO-DD  
INN  
Official Name English
BENZPHETAMINE [VANDF]
Common Name English
BENZPHETAMINE [MI]
Common Name English
BENZENEETHANAMINE, N,.ALPHA.-DIMETHYL-N-(PHENYLMETHYL)-, (.ALPHA.S)-
Common Name English
BENZFETAMINE [WHO-DD]
Common Name English
(+)-N-BENZYL-N,.ALPHA.-DIMETHYLPHENETHYLAMINE
Systematic Name English
BENZPHETAMINE [HSDB]
Common Name English
BENZFETAMINE [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29728
Created by admin on Fri Jun 25 23:07:50 UTC 2021 , Edited by admin on Fri Jun 25 23:07:50 UTC 2021
DEA NO. 1228
Created by admin on Fri Jun 25 23:07:50 UTC 2021 , Edited by admin on Fri Jun 25 23:07:50 UTC 2021
NDF-RT N0000175372
Created by admin on Fri Jun 25 23:07:50 UTC 2021 , Edited by admin on Fri Jun 25 23:07:50 UTC 2021
NDF-RT N0000175651
Created by admin on Fri Jun 25 23:07:50 UTC 2021 , Edited by admin on Fri Jun 25 23:07:50 UTC 2021
LIVERTOX 97
Created by admin on Fri Jun 25 23:07:50 UTC 2021 , Edited by admin on Fri Jun 25 23:07:50 UTC 2021
NDF-RT N0000175372
Created by admin on Fri Jun 25 23:07:50 UTC 2021 , Edited by admin on Fri Jun 25 23:07:50 UTC 2021
NDF-RT N0000175423
Created by admin on Fri Jun 25 23:07:50 UTC 2021 , Edited by admin on Fri Jun 25 23:07:50 UTC 2021
NCI_THESAURUS C47795
Created by admin on Fri Jun 25 23:07:50 UTC 2021 , Edited by admin on Fri Jun 25 23:07:50 UTC 2021
Code System Code Type Description
DRUG CENTRAL
329
Created by admin on Fri Jun 25 23:07:50 UTC 2021 , Edited by admin on Fri Jun 25 23:07:50 UTC 2021
PRIMARY
RXCUI
1422
Created by admin on Fri Jun 25 23:07:50 UTC 2021 , Edited by admin on Fri Jun 25 23:07:50 UTC 2021
PRIMARY RxNorm
ChEMBL
CHEMBL3545985
Created by admin on Fri Jun 25 23:07:50 UTC 2021 , Edited by admin on Fri Jun 25 23:07:50 UTC 2021
PRIMARY
HSDB
3294
Created by admin on Fri Jun 25 23:07:50 UTC 2021 , Edited by admin on Fri Jun 25 23:07:50 UTC 2021
PRIMARY
MERCK INDEX
M2391
Created by admin on Fri Jun 25 23:07:50 UTC 2021 , Edited by admin on Fri Jun 25 23:07:50 UTC 2021
PRIMARY Merck Index
EVMPD
SUB05748MIG
Created by admin on Fri Jun 25 23:07:50 UTC 2021 , Edited by admin on Fri Jun 25 23:07:50 UTC 2021
PRIMARY
DRUG BANK
DB00865
Created by admin on Fri Jun 25 23:07:50 UTC 2021 , Edited by admin on Fri Jun 25 23:07:50 UTC 2021
PRIMARY
INN
978
Created by admin on Fri Jun 25 23:07:50 UTC 2021 , Edited by admin on Fri Jun 25 23:07:50 UTC 2021
PRIMARY
NCI_THESAURUS
C61647
Created by admin on Fri Jun 25 23:07:50 UTC 2021 , Edited by admin on Fri Jun 25 23:07:50 UTC 2021
PRIMARY
EPA CompTox
156-08-1
Created by admin on Fri Jun 25 23:07:50 UTC 2021 , Edited by admin on Fri Jun 25 23:07:50 UTC 2021
PRIMARY
CAS
156-08-1
Created by admin on Fri Jun 25 23:07:50 UTC 2021 , Edited by admin on Fri Jun 25 23:07:50 UTC 2021
PRIMARY
FDA UNII
0M3S43XK27
Created by admin on Fri Jun 25 23:07:50 UTC 2021 , Edited by admin on Fri Jun 25 23:07:50 UTC 2021
PRIMARY
PUBCHEM
5311017
Created by admin on Fri Jun 25 23:07:50 UTC 2021 , Edited by admin on Fri Jun 25 23:07:50 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY